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2-tert-Butyl-1,1,3,3-tetramethylguanidine → 4-(3,3-Difluoro-cyclobutylamino)-5-methanesulfonyl-2-methyl-benzoic acid methyl ester

HRID 1815460
Notes
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Reaction equation

HRID 1815460 reaction equation
[F:1][C:2]1([F:11])[CH2:5][CH:4]([NH:6]S(C)(=O)=O)[CH2:3]1.[CH3:12][O:13][C:14](=[O:27])[C:15]1[CH:20]=[C:19]([S:21]([CH3:24])(=[O:23])=[O:22])[C:18](F)=[CH:17][C:16]=1[CH3:26].C(N=C(N(C)C)N(C)C)(C)(C)C>CN1C(=O)CCC1>[CH3:12][O:13][C:14](=[O:27])[C:15]1[CH:20]=[C:19]([S:21]([CH3:24])(=[O:22])=[O:23])[C:18]([NH:6][CH:4]2[CH2:3][C:2]([F:1])([F:11])[CH2:5]2)=[CH:17][C:16]=1[CH3:26]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 35715812-tert-Butyl-1,1,3,3-tetramethylguanidineHCID 10538364Methyl 4-fluoro-5-methanesulfonyl-2-methylbenzoateHCID 22500956n-(3,3-Difluoro-cyclobutyl)-methanesulfonamide

Product 1

HCID 698087234-(3,3-Difluoro-cyclobutylamino)-5-methanesulfonyl-2-methyl-benzoic acid methyl esterYield 17.5%

Reagents, catalysts & solvents 1

HCID 13387
N-methyl-2-pyrrolidone
Solvent

Conditions

Temperature
150 °C

Procedure

0.70 g of N-(3,3-Difluoro-cyclobutyl)-methanesulfonamide, 0.93 g of 4-fluoro-5-methanesulfonyl-2-methyl-benzoic acid methyl ester, and 1.5 ml of N″-tert-butyl-N,N,N′,N′-tetramethyl-guanidine were dissolved using 10 ml NMP (anhydrous) and stirred for 6 h at 150° C. The reaction mixture was cooled to ambient temperature and 200 ml of EE added. This solution was washed three times using 20 ml of a saturated aqueous NaHSO4-solution each time. Thereafter, the organic layer was washed three times using 30 ml of a saturated aqueous Na2CO3-solution each time. The organic layer was dried over MgSO4 and the solvent removed in vacuo. Chromatography on silica gel using DIP yielded 220 mg of a colourless foam.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. addition200 ml of EE added
  3. washThis solution was washed three times
  4. washThereafter, the organic layer was washed three times
  5. dry with materialThe organic layer was dried over MgSO4
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-6fd7de97231d49aaadb4d63c23af7c18
Source dataset
uspto-grants-2005_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06878748B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes